Hydrochloric Acid → HCID 178437574, compound

HRID 1523278Notes

Reaction equation

HRID 1523278 reaction equation
CC(S([NH:7][C:8]1([CH:12]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[N:18]=2)[CH3:13])[CH2:11][O:10][CH2:9]1)=O)(C)C.Cl.C(=O)([O-])O.[Na+]>CO.O1CCOCC1>[F:29][C:26]([F:27])([F:28])[O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:18]=[C:14]([CH:12]([C:8]3([NH2:7])[CH2:9][O:10][CH2:11]3)[CH3:13])[NH:15][CH:16]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 178437575HCID 178437575, compound

Product 1

HCID 178437574HCID 178437574, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-methyl-N-[3-(1-{4-[4-(trifluoromethoxy)phenyl]-1H-imidazol-2-yl}-ethyl)oxetan-3-yl]propane-2-sulfinamide (Preparation 9, 0.320 g, 0.74 mmol) in methanol (4 mL) at 0° C. was added 4M hydrogen chloride in 1,4-dioxane (4 mL) and the reaction left to stir for 2 hours. Solid sodium hydrogen carbonate was added to the reaction, followed by a saturated aqueous solution of sodium hydrogen carbonate. The mixture was extracted with dichloromethane. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the title compound (0.243 g, 91% yield).

Workup

  1. waitthe reaction left
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-139511fa21994bf5b255144198486d53
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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